


Sometimes

by JamieWinchester



Category: Supernatural
Genre: BDSM, Bondage, F/F, F/M, I should never be allowed reading fanfiction, Kinky, M/M, Multi, Near incest, Porn, Sex, filth pure filth, it inspires things, there are no bounds really, this is a horrible abuse of everyone
Language: English
Status: In-Progress
Published: 2016-12-31
Updated: 2017-03-12
Packaged: 2018-09-13 18:49:52
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con, Underage
Chapters: 6
Words: 12,652
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9136951
Author URL: https://archiveofourown.org/users/JamieWinchester/pseuds/JamieWinchester
Summary: Inspired by Amazonia_8's, stamp your passport.Anyways, when Castiel meets someone on a island, he realizes his life's not working, and thigns start blowing up in his face....but sometimes, things have to fall apart to come back together. and with his whole life on the line, Castiel tries to achieve the one thing he wants....to be happy.





	1. Chapter 1

**Author's Note:**

  * Inspired by [All Inclusive K!ink](https://archiveofourown.org/works/4919200) by [Amazonia_8](https://archiveofourown.org/users/Amazonia_8/pseuds/Amazonia_8). 



> like I said, it's inspired by Amazonia_8's Stamp your passport series, especially the first called All inclusive kink. Anyways, I'm going to try and be better about posting, but I make no promises, this is just my stress relief when I get time to write and motivation to do so.

Castiel Novak frowned slightly as he followed his cousins through the halls of the hotel, flushing a little as he looked around. Balthazar and Gabriel had simply said trust them when they’d packed his bags for the week and told him to get in the car. The fact that he’d been so miserable mere days before his birthday, that he hadn’t even questioned where they were going until now was a disturbing thought to the 29 year old, considering every childhood trauma and trouble he’d gotten into, had started with the words, “[I]Hey Cas, trust me.[/I]

The dark haired artist looked tired, worn around the edges like a fading photograph. Yet, while he looked younger then his soon to be 30 years, the knowledge that he was never going to get to do what he wanted again, would never have the peace and quiet of locking himself into a studio for hours at a time, and simply draw until the story was done was hurting him. The fact that the project that had been his for years, a book that had been consuming more and more of his time as he fleshed it out, developed the story, would never see the light of day again just made him sad. Even if this wasn’t the relaxing trip he’d been hoping for, he was sure his cousins had his best interests at heart, and they’d be doing something he wanted to do.

“I love this place.”Balthazar said as he glanced back at the youngest of the three best friends, watching Castiel look around him. Smirking slightly, knowing that Sabian’s was going to be perfect for Castiel. The island was in the middle of the Atlantic, far enough south that it had warm and mild weather for most of the year, and was definitely a plus when so many people enjoyed being naked on the island. It was a home to every kink and sex act the imagination could think of. Offering classes, orgies, clubbing, and anything under the sun that the heart could desire, it was perfect get away from the world for those who enjoyed sex. Which wasn’t Castiel. Cas, who’d been invited simply because he was something beautiful and amazing to the people of Sabian’s. Innocent. Not that the poor miserable artist knew that, but Balthazar knew he’d discover it soon enough.

“.….”Castiel frowned staring at the people wandering the halls as they made their way to their bedrooms, pausing in the entrance hall to look at Gabriel and Balthazar. “What did you two do?”

Gabriel snickered a little because he really hadn’t thought it’d take him that long to ask. Or that easy to not only get him in the car, but the airplane and island to get here. It had been slightly sad to see the man trailing after them like a sad and abandoned puppy. “You’ll find out tonight after it’s to late for you to back out.”Gabriel teased, mostly because it was already to late. 

“Cas, have we ever led you wrong?”Balthazar teased, smiling at him. Out of the entire Novak clan, only Gabriel and Balthazar had never purposefully lied or trick Cas in some manner. Granted, they’d hurt Cas’ feelings time to time as all kids did, but they were always apologetic. “I think this exactly what you need, and you don’t have to be a active participant.”

“You can say no, you don’t have to do anything….just give it a chance, okay?”

“That doesn’t reassure me any. You love alot of things that most people wouldn’t touch with a ten foot pole.”And while coming from any other Novak the words would ahve been a scathing indictment of Balthazar’s lifestyle, from Cas, who more then anything just wanted to be left alone, it was a gentle tease. “And yes, you go me arrested once for being drunk and flashing my neighbors. And…all the times I’ve been arrested was because of you two.” Not that twice for public indecency and intoxication was alot but he liked giving them a hard time about it when he was feeling in over his head. Eyeing his cousins he sighed a little, because at the end of the day, he trusted them. “…”

“Now, we all have separate rooms, it’s a rule. Not even married couples share. If our doors are open come on in, if they’re closed I’d recommend staying out unless you want to see your cousins in various sides of coitus.”Gabe snickered motioning Cas to follow them into the large, luxurious bedrooms that were, more or less sound proofed so no one would disturb the others. “This ones yours. Settle in, get something to eat, relax until later. Then we have to head downstairs for opening speeches.”

need help getting laid, you two. You know that right? I’m getting married in a week, I’m perfectly capable of doing things on my own.”Cas said as he heard about interrupted sex, having a perfectly good idea what kind of place they’d brought him to, sighing softly. 

“There’s other features here to, like a full spa, if you want. This isn’t about getting laid, Cas, not really. This is about you getting the chance, before you never get a chance again.”Balthazar said watching his cousin, shrugging a little. “And you don’t have to participate but at least you can see, watch, experience and have a chance to enjoy yourself. Just….give it a chance.”

“We’re doing this because you being married in a week, this is your last chance to be who you want to be. We figured it’d be better for you to have some good memories before Chuck fucked up your life.”Gabriel said sighing quietly as he watched his cousin settling onto the couch, leaning down to press a kiss to his forehead. “Relax. Eat. We’ll be back later.”Gabriel promised even as he headed for the door, smirking at Balthazar. “So, did you hear the Winchesters are back, and teaching this year?”

Castiel stared after them, wondering why sex would need teachers.

* * *

Sam Winchester snickered silently to himself as he tossed his bag onto the porch of his small beach bungalow, before crossing the small bridge to dean’s. pausing on the bridge to marvel at the island’s beauty once again, he smiled slightly as he ducked into Dean’s living room, taking in the soft plush couch, and staring down at the floor for a moment to orient himself. No matter how many times he saw the teacher’s rooms-even if this was his first time teaching himself- the glass bottoms to the living room straight down to the ocean still disoriented him some. “It amuses me that you volunteer to come here, when you know it involves flying.”Sam teased as he tossed himself onto the couch with a careless klutzy grace of a man who was just to big sometimes, and had long given up trying to be as graceful as Dean.

The moose of a man was tall and fit, all sleek lines and built solid. The fact that he looked like he’d just stepped of a runaway, or maybe a college campus, boot cut jeans and a dark t-shirt with a soft scarf absently tossed around his neck to hide the hickeys that were from the night before. His dark hair was soft and wavy, tied back into a small ponytail, he looked soft. Yet of the two of them, Sam was the brutal one to keep in bed most of the time, willing to tread a very fine line between enough and to much. The look was there, but Sam Winchester was anything but soft. Growing up with a alcoholic father and a dead mother, with only Dean around to look after him, had taught him early to look after himself.

“Says the guy who has to hesitate before he’ll set foot in my living room.”Dean teased, looking amused. “How hungry are you?”Dean asked as he flipped a pancake with practiced ease as he checked his phone, making sure no one had called him with a emergency. He ran a dog breeding farm, and while he’d taken the week off, he was on call in case something had gone wrong. Glad to see there was no texts or calls he smiled slightly as he considered the question. It was so normal for him to look after and fuss over Sam, that even here, he looked after him. 

“It’s weird walking on it. And very.”Sam said.

“Anyone catch your eye on the boat at all?”Dean asked curiously as he tossed a plate of pancakes in front of his brother just the way the other liked them. “Did you hear Crowley invited a kink virgin to the island? I wonder how true that was.

“Hm, Novak’s back for another year so I’ll probably snag him for a bit.”Sam said looking amused as he considered Gabriel novak, because they’d been circling each other for years, and yet had never had sex. They’d scene with Dean being in control and a few others, but never just them and Sam was going to see just how desperate he could leave the man and see if Gabriel wanted him just as much. “Thanks.”He added as he started eating. “And I heard. I can’t wait to see if it’s true. And who the innocent came with.”Well aware that if there was indeed a kink virgin on the island, someone had invited them, brought them to Crowley’s attention. “You should see about finding the virgin first, so you can get your rocks off with them first.”Sam teased well aware of Dean’s virgin kink. His brother had a weakness for sweet innocents. 

“You know, he’s getting desperate. If you don’t fuck him this year, he’s going to end up kidnapping you from your own home.”Dean warned looking amused. “And I wont help you because you’ve been the biggest cock tease in the world.”Dean chastised before smirking. “I’ll die if I get my hands on that sweet virgin first.”Dean admitted licking his lips as he scarfed down his food, glancing at the clock. “Come on, we got to go before we’re late.”

“You better not die if you get to him first.”Sam snickered as he followed the other out of the room, rolling his eyes as he watched dean strip off his shirt. Amused as he saw the tattoo high on one pectoral and nipple and belly ring glinting in the low light. It highly amused him that Dean was so obsessed with Supernatural, the ever popular comic book he’d been reading for years, and was currently sulking over because the author was ending the series. Rubbing a hand over his face as he watched Dean go for a moment, before shaking his head, following after him as he started stripping out of his own clothes, knowing there’d be a place to leave them when they got to the banquet hall.


	2. Chapter 2

“See them?”Gabriel asked his cousin as they stepped into the dining hall, tilting his head towards the hulk of a man and the slightly smaller one reclining in their own chairs near the front. “Those are the Winchesters. They’re legends. They’ve both been coming here since they were legal. Back when they started, you could come in at 18, but now because of the alcohol, you have to be 21…They’re the two new trains. Dean, the slighter one, he’s taking three classes for his first time, most people only do one or two. And that’s Sam, and I’m going to stalk him until he fucks me or so help me god, I’m following him home.”

“You would be like the world’s worst puppy, no wonder he wont let you follow him home.”Cas muttered snorting amused as they settled into their chairs, glancing at Balthazar when he spoke. 

“That’s Crowley, talking to them, he’s the owner. What he says here is law and no one is going to argue with him. Make sure you pay attention when things start.”He said settling in to wait.

* * *

“Look. They have someone new sitting with them, looks like a sub, maybe Gabriel got tired of waiting for you and snagged his own partner already?”Dean teased smirking at Sam a little, looking around, picking out all the new faces, trying to figure out which, if any, was the kink virgin.

“He does look like a sub. So maybe he’s Balthazar’s. Gabriel’s totally not domming anyone.”Sam snickered a little though he was a little worried about that. He sighed softly turning to look at Crowley as he started to talk.

“Now, I know what some of you first timers are wondering why we’re not going at it yet. We will, I assure you, just a few rules first. Those of you returning, know that everything has been outlined in your contracts, but since I’m fairly certain me and Sam here are the only ones who’ve read the whole thing-”Crowley snickered quietly glancing at the lawyer at his side before focusing on the others. “You get to hear them all. Now. Rule number one, I’m in charge, and you’ll all show me due respect. My word is law. However, I wont stop or alter a scene as long as it’s safe, sane, and consensual. While you are here, you will all use the color system for check in. I don’t have time to sort out everyone trying to use different systems, so use this. Clear?”

“Yes!”Came the cheerful replay. 

“Now, I will have people round monitoring and looking after everyone, so if they ask you anything, you will stop and answer them. If anyone feels unable to communicate with their partner or needs something addressed, my pets are an extension of me and I will be giving serious thought to what they find. In each room you will find a tablet to use to browse the list of guests and send requests as you wish. Doms you may have noticed your claim tags, any submissive wearing a tag is unavailable to scene with another until they take it off. Subs, I’m sure you know, but I want to make it clear right now, you are under no obligation to scene with anyone you don’t wish to. I wont tolerate any high school bullshit of pressuring or forcing or any stupid shit. Clear?” He paused for a moment listening to them answer before smiling. “Now remember, all subs and doms are to wear their gifts, that is, their collars, whenever they’re in public or with a dom or sub in private. They will be found with your tablets in your rooms. All interactions with one another must be sober. No go have fun. Mingle. The game begins at midnight.”

* * *

“Well….looks like the little Sub is annoyed.”Dean mused with a smile, tilting his head as he watched the dark haired beauty slug Balthazar in the arm without looking, hard enough the man yelped. “Looks like you were right. Zar’s the one who claimed him, or brought him. Grinning wider even he realized he’d been right, the beauty was wearing a collar. 

The doms had arm bands, that could be worn around the upper arms, forearms, or wrists as they pleased. Dean was already wearing his around muscular upper arms, his shirt off so the world could enjoy the angel wing belly button ring he was wearing, in the soft perfect lighting. He’d stople it from Lisa, but she hadn’t tried to steal it back so it was his for keeps now. His nipple ring was a simple hook which he’d attached a tiny angel wing pendant to.

Sam snickered a little watching his sibling, amused that Dean already looked well on his way to claiming the dark haired man, and wondering just what kind of trouble he’d get into. His eyebrows creeping up as he watched both his wife and lisa making their way towards the sub making his way out of the room.

* * *

“Jared?!”Lisa bounded over towards Cas, eyebrows raised. “It IS you! I didn’t know you did kink.”She admitted with a smile. “Don’t worry, I wont tell. This is your first time right? You have to let me show you around!”She ordered before laughing at Jess’s huff. “You can come to of course, I wont never have sex without you.”

“Hello Ladies.”Cas winced, his shoulders hunching up around his ears a little before he sighed, lowering them as he turned to face the girls. “And I don’t. apparently this is the world’s worst birthday party given to me by idiots.”Cas made a face, even if the tone wasn’t angry or truly upset, simply exasperated and tired, he really should have known something like this would be what they’d planned.

“Wait. You didn’t know what this place was?!How did you even get on the island? Crowley  
S a major one for background checks, I don’t know if I’ve ever heard of anyone being here without knowing exactly what they were in for…..well, whoever brought you here must have thought you’d find some relazation or enjoyment. If nothing else than for the free boobies. Plus the rooms are amazing, you can walk around completely naked if you want. Stick around, you might learn something about yourself.”

“Nope. And by knowing idiots, who seem to think turning 30 is something to celebrate.”

“I just can’t believe you came out of your house without me having to drag you. You have to come meet my boys.”Lisa ordered dragging Cas off by his arm, not even noticing Balthazar and Gabriel were staring after them, amazed that Cas didn’t seem bothered by Lisa or Jess in the least. 

“I leave my house a perfect amount of time, lisa. On my own.”Cas said.

“You don’t leave the house unless it’s to walk that monster cat of yours.”Lisa scolded before grinning. “Dean!Sam!”Lisa crowed snickering. “This is Jared. Isn’t he adorable?”

“Very.”Dean agreed with a sly grin. “Would you like something to drink, Jared?”Dean asked before ordering. “Lisa, you slut, he’s losing the feeling in his fingers, loosen the grip a little.”

“Water would be fine….and yes, bitchling, if you want me to keep working for you, you have to let my arm go.”Cas said, his eyes going wide at the normal insult, flinching slightly. The words, the usual insult so commonplace that they’d come out before he’d remembered that ‘Jared Ackles’ was dying in a week from today. “Lisa?I think you better start calling me Cas now. I think you deserve to at least know that.”He corrected gently, ignoring Sam’s sharp interested gaze. “Anyways….I better be going…thanks for saying hi, jess. Lisa.”He said gently pulling his arm away, wondering how he was going to keep up the friendships that mattered to him, when things changed.

Dean nearly choked on his gum at the the insult, looking amused. Not many had the guts to call lisa names. “Cas?”Dean raised his eyebrows.

“Jared?Are you alright?”Jess asked moving to Sam’s side, leaning into him a little as she watched her friend. 

“Yea. It’s the name on my driver’s license….and I’m fine.”Cas muttered.

“You have your driver’s license?Then why do I come to you?”Lisa demanded, looking annoyed.

“Because I don’t have a car.”Cas shrugged a little before startling at the very british, posh and delighted voice that sounded behind him. 

“Did someone say Cas?”

“Crowley, you still haven’t gotten me your manuscript, naught man!”Lisa chastised him making Crowley chuckle and patted her on the head. “It’s a work in progress my dear. So your Cas? I must say, it’s a delight to have you. I’ve never had one before.”Crowley smirked looking him over. “A pure kink virgin, how exciting.”

Dean swallowed thickly, instantly hard and fascinated, breath hitching as he studied Cas even more intently then he had been. “Dibs.”Dean said before flushing hard as he realized he’d said it out loud. “Sorry… didn’t meant to say that out loud.”He muttered making both Sam and Jess snicker.

“I’m not a virgin?!Why does everyone assume this!”Cas scowled looking annoyed and upset, not understanding what they were talking about, and fairly annoyed with it all. It was adorable just how innocent he really was. Scowling as he stepped back. “I better be going…I’ll see you later…”He said bolting towards the door. Having every intention of locking the door behind him and staying inside to draw and work the whole time he was stuck here.

“.…Not if I get to him first.”Sam said, swallowing thickly as he stared after Cas, reaching down to adjust himself. “He’s innocent?Like…completely?Seriously?”He asked after a moment, sounding utterly enthralled at the idea. He figured the man wasn’t a virgin, but the way he’d bolted, said it wasn’t more then that.

Dean growled spinning on his heel to stare at his brother. “I have never used the big brother card on you, Sam, but I fucking swear to god if you take this away from me I will never make you food ever again of any kind.”

Sam winced at that, “Mean.”He grumbled even if he nodded, as much as he’d enjoy fucking the virgin, it made him twitch at the idea of never having dean cook for him again. He’d probably starve if he had to go without having dean cook for him. Even married, dean did most of his and Jess’ cooking.

“Completely. He’s had sex, if you can call it that, but nothing anymore more exciting then 69ing if his applicants are to be believed.”Crowley admitted with a snicker as he watched dean heading for the door.

“Wow.”Sam muttered looking amazed before tilting his head, frowning slightly. 

“Yes, indeed. I almost didn’t allow him in. It’s a bit of a hazard having someone so fresh on the island. But his cousins pleaded his case. Apparently the poor boy is being controlled and forced to go into the family business.”Crowley made a face. His use of the world controlled was key, because it meant ‘Jared’ was one of those unfortunate souls who was choosing approval of his family over his own personal happiness and wealth. 

“Sam. Where’d dean go racing off to?”Gabriel said as he and Balthazar joined the other men.

“He’s chasing after the cute little virgin. I wouldn’t expect to see him before tomorrow.”Sam said watching Gabriel. 

“Ah, well no one better for our precious Cassie.”Balthazar snickered, not bothered by the idea of Dean with CAs. Dean was a good man, even if he didn’t always see it himself, and he was good with virgins and innocents. “So I heard Dean needs some help with his classes? Maybe I’ll lend a hand? He’s doing the seminar on shibari and light pain play right? Maybe I’ll let him hit me. Could be fun.”Gabriel snickered, vying for a reaction from Sam.

“Well, I’m sure your cassie is going to get more of dean’s attention then he ever wanted. You know he has a kink for innocents.”Sam snickered quietly because Dean was so good with newbies. “And if you’re lending a hand to anyone’s classes, it better be mine, Novak.”Sam said wrinkling his nose, a little possessive glint in his eyes as he studied the other.

“Anyways, we should go get some attention.”Gabe admitted looking at balthazar. “I wanna get laid. I’ve been horny for over a month now.”

Sam growled softly, reaching out, fingers closing around the other’s collar, tugging him close, careful not to stab himself on the spiked collar gabe had chosen for himself. “Were you thinking of having anyone’s attention but mine?”

“I don’t see your tag on my collar, Winchester.”Gabe sniffed, tossing his head a little. It was one of the many ways Gabe ‘displayed’. he was tired of playing nice. He was going to make Sam work for it. He’d flipped the tables, if Sam wanted him, then Sam was going to have to be a hunter, because Gabe was going to run and if Sam didn’t chase then Gabe was moving on. It had been five years, Gabe was done playing. “And well, you’ve never shown a true interest before now, I’m thinking maybe your just a cock tease. More bark than bite. All words and no action, limp dicked.”Gabe taunted and both Crowley and Balthazar excused themselves because he really didn’t want to be caught in this fight that’d everyone knew had been coming.

“You of everyone here, know that a limp dick isn’t my problem, pet.”Sam said easing to his feet, crowding into the other’s space, holding up a tag. “Now, are you going to volunteer for my class tomorrow, or am I going to have to find a cute little brunette who’s actually submissive, instead of your pain in the ass topping from the bottom?”Sam asked, wicked amusement in his eyes and he was torn between really chasing gabe, or letting him go.

Gabe narrowed his eyes at Sam, tilting his head proudly for a moment, looking as if he was about to refuse to submit, then nodding, letting the other clip the tag on. “I would be delighted to help you with your class tomorrow.”

“Good, cause I have plans that fit so much better with you, than anyone else.”Sam muttered stealing a kiss, well aware he was driving the other to distraction, and had been for years. Even knowing the other knew about his fascination, he usually refused to discuss it with anyone, even Jess. “Now. Do you have plans for the evening?Because I have this awesome new room that’s just asking to be broken in.”He said.

“I have a meeting in a half hour but it shouldn’t last longer then ten minutes. I’m completely free after that….and make sure to make room in your busy schedule to talk. Because we’re going to talk.”He promised as he turned to leave. “And you better be there Winchester, or I’m gonna go find that cute brother of yours!”He teased as he flounced away, leaving a bemused Sam staring after him.


	3. Chapter 3

“Can I come in?”Dean called pausing to knock on the door that had just been pushed shut. “Just to talk? I wont touch without your permission.”Dean added, going still as he waited.

Inside, Cas turned away from where he’d been digging into his bag, pausing as he considered the door. The tablet in his hands almost held like a shield between them as Cas opened the door before shrugging. It had hurt a little, and he was feeling like he’d stepped off and into a very confusing place, but he had always been well aware that people thought he was weird, a little odd. So the fact that they did to, really didn’t bother him…..except it did.

“You looked confused and kind and hurt, and I was hoping I could help?”Dean offered. “We weren’t trying to be mean, it’s just around here, ‘virgin’ means something different. It just means someone who’s never done kink before that’s all. We weren’t trying to be cruel.”

“No….I’m sorry. I overreacted….I’ve been having a long week…it’s…whatever.”Cas shrugged, swallowing thickly as he looked over the good looking man standing in front of him. Half tempted to invite him in for a night of mindless sex to forget what his life was becoming, but he was confused on what would be asked of him, he was in a place he didn’t know anything anymore, and didn’t want to ask either. “Come on in. Do you want something to drink?”

“No, you didn’t overreact. We were being insensitive. In a place like this, that can have devastating effects.”Dean said as he stepped in, nodding. “’I’ll take a soda.”he said taking the can when the other handed it to him, tilting his head as he watched him.

Cas frowned a little not sure what to say to that….that his feelings mattered here. There were only a few people in his life that actually cared how he felt, and in the last two months as he stared down the barrel to his birthday, he’d felt things crushing him. For a moment though, he felt lighter. As if the simple acknowledgment that he mattered, that how he felt, mattered it made a difference.

Easing down onto the couch as he sighed, Dean smiled. “Virgin, in this case, means you have no experience. Whatever-soever in anything that goes on in the world of kink. It means you don’t know the rules, the etiquette, or the effects and we have to be slower, gentler because you wont know what to expect. People new to kink, no matter their personality or attitudes, are ususally very timid when faced with their first time and we have to be prepared for that as well. In truth, physical status of virginity barely matters in a place like this. Makes sense? And emotions are so important because the heightened state of mental being that both doms and subs fall into when engaging in kink. A wrong word can throw us off. I spent a afternoon crying in my room once because someone said I was ‘pathetic’ when I was to high on endorphin…it’s perfectly normal to feel scared and upset, but your excited to, right?”

“...I feel stupid now, for both running off, and cause apparently I didn’t ask enough questions when Gabe told me to get in the car.”Cas growled sounding annoyed with himself that he hadn’t questioned more, even as he stripped out of the hoodie he’d been wearing before moving to sit in one of the reclining chairs, curling up like a kitten in it. The black t-shirt hugging a well defined body, despite his stationary life, the man worked out. A wide leather watch covered his wrist, and while it obscured it mostly, the edges of a freshly inked tattoo showed around it, so freshly inked it was a little red, and it had to be killing him to have the watch over it. Maybe he was more aware of liking pain then everyone had thought. “….Yes…it makes sense.”Though he really didn’t understand it, he could get a beginnings of why it mattered, and why Dean had come to explain. “And thank you for coming to explain….”

“You’re not stupid, or weird. You’re not something to be ashamed of. Just keep one thing in mind okay? It’s okay to feel the things you feel. It’s okay to like the things you like, even if you end up not liking kink, or only like a bit of a slap and tickle, that’s okay. Some people take years of self doubt and personal disgust before they realize there are others like them, that it’s not wrong, not disgusting….it’s natural and normal, and more common then people would think.”

“.…Even if I don’t feel anything at all?Usually?”He corrected after a moment of thinking about it. Because it wasn’t that he didn’t like having sex, or even wanted to stay celibate, he ust normally didn’t find someone who turned his crank most of the time, and if he did, no one had ever inspired him to make the effort for more then one night, simply getting the biological need out of the way before returning to his art.

“Hm, lack of sexual interest? That’s a bit more rare, but again not all that uncommon. There are a number of people who are asexual, meaning they find no sexual interest in anything, or demisexual, meaning they have to be romantically invested before they feel sexually attracted. There are others to but it tends to get extremely complex. It could be as simple as stress related sexual inhibition. Meaning if your stressed your not sexually inclined. It’s all normal still. Even if some claim to be normal say otherwise. In truth they’re just repressing and taking it out on others for a lack of a more appropriate target.”Dean said watching the other settle in, glad to watch him relax and really think about it. 

“You really are gorgeous.”Dean said watching the other, before examining him more, waving a hand at him,”May I?”He asked indicating the watch and gently taking the other’s hand as Cas held his hand out. Examining the red skin at the edges as he took the watch off, “You have to be careful with things like this. You can bruise, or even tear the skin which will mar the tattoo or cause infections…pain is fine, actually damaging yourself isn’t okay….so, not as much of a virgin as we thought if you know you’re submissive and you like pain.”

“I know. I have a few, and there’s a bandage under there.”Cas said smiling slightly as he watched Dean pull off the watch and bandage, staring down at the angel wing and knife overlaying it. Relaxing a little as he realized it really was okay, before shrugging a little. “The collar was waiting for me on the dresser….I figured I was supposed to wear it. And the pain is grounding….makes me not think of things.”

“Well, I have some cream in my room for abrasions that should help. It’s got antibiotics and lotions, keeps the skin nice and flexible as it neals. It’s very well done to.”Dean said touching it gently. “Leave it uncovered for awhile and I’ll get the cream in awhile, and if the swelling has gone down in the morning you can put the watch back on.…pain can be very grounding and calming if down correctly. I’d really suggest coming to my ‘light pain’ seminar to. A lot of people don’t realize this, but there are safe ways to hurt yourself. It’s not recommended but it can be done if there’s no other options.”Dean said looking his arms over, pleased to see no cutting scars. “The collar marks you as someone who prefers to be hit, on the bottom, take it up the ass…things like that. What it truly means, is up to you.”

“Thanks, that’d be nice.”He said thinking about it really, relaxing, considering what dean was telling him.

“So….how would you feel about maybe, trying something simple with me?”Dean asked watching the other. “I mean, you came all this way right? And I’m not that bad looking, know what I’m doing, it’d be worth a shot right? I’m teaching a class in the morning to, about bondage and shibari if you want to come.”He added with a smile. “It’s a sort of mild class for beginners and experts alike so I’d be delighted if you came?”

“...no. You’re not bad looking.”Cas agreed going quiet as he watched the other. Nodding slowly. “Okay….and I’ll come to class.”

“Well, thank you. You’re very nice yourself. This is a claim, where you listening when Crowley explained what these where? I’d like to do a scene with you.”Dean said smiling. “Something easy, something….that I think you’d really like. What do you say? You can always say no, even in the middle of the scene, and you should always stop if you feel upset or strange or have any hesitancy.”Dean said watching him. “Communication is key, and you should always speak up if you feel anything negative at all, even if your not sure why.”

Cas smiled, flushing a little at the other’s praise, ducking his head a little before nodding. “And okay…let’s try. And I’ll remember to speak up if something happens…but I want to try.”

“Okay.”Dean said grinning as he got up from the seat he was in, moving over to stand in between the other’s legs, smiling slightly as cas’ legs closed just enough to brush against him, leaning in to slip the metal tag onto the other’s collar, leaning in to kiss him slowly, gentle and careful before straightening. “Now, I have this lovely idea. Do you want to hear it?”

“Yes, I want to.”Cas growled softly, sounding sulky and grumpy, the other kept asking him when he kept answering the same, he wanted to hear. Even without training, without really knowing what was happening, the cute little sub was being adorable and sulky, acting out even if he wanted this.

“Good.”Dean teased with a grin, amused at the other’s sass and grumbling.”I like to tease, you see. So I thought, perhaps, I’d tease you all night long.”Here a smirk twisted his lips. “Or maybe, make you tease yourself. What do you say, Jared?”

“.…Cas. Not jared. Please.”Cas corrected sighing softly. “I just write under Jared.”He said rubbing a hand over his face, because he remembered what dean had said, that he had to share what he was, and correct it if things felt wrong. And Hearing Jared, messed with him. Knowing that if he let it go, it would mess him up even more. 

“Cas, then.”He agreed with a smile, stealing a kiss before watching Cas really consider what he was hearing.

Cas tilted his head slightly as he really considered what Dean wanted to do.“Sounds interesting.”He said sounding nervous at the idea, even as he looked up at the other, his eyes dark and dilated, definitely interested.

“Very interesting. I want you to touch yourself, I can watch you, through the tablet. Or I could stay and just watch you, though I dunno if my self control would last. I want you to fondle yourself, tease yourself, every hour but your not allowed to come. And in the morning, when your so desperate you want to cry, I’ll come and fuck you with all the passion you desire.”

“...I can do it myself…and alone but…”Cas bit his lip, thinking it over, beacause he wanted to but…”And if I get upset or anything, you could come back….”He said after a moment, shuddering. “Okay. I can do this.”He said looking pleased and happy with the task, even if it wasn’t something he normally would have done.

Dean grinned at how eager the other was. “You’re perfect you know that?”He said running his fingers through the other’s hair. “And yes, I’ll monitor you constantly. When this light glows bright blue, it means I’m connected and watching.”Dean said as he picked up the tablet, showing the other where the light would be. “I wont close down the connection and if you need me at any time, you only have to say yellow, or red, or use any other method to gain my attention. Asking for help, asking for me, telling me you can’t do it, or can’t handle it will summon me instantly to your room. Even if you say nothing and you show signs of distress I’ll likely come personally to check on you anyway.”Dean said studying him. “You just like the idea of being challenged don’t you?”

“Okay…..and I do. I’ve made a life of overcoming the challenges in front of me. It sort of appeals to me to do it in my sex life.”Cas said kissing the other as Dean leaned close for a kiss. Relaxing at the idea that even if he forgot, didn’t say anything and dean would come if he needed anything.

“Remember, I’m just a shout away if you need me. Touch yourself, get naked, put on a show. The more you make me squirm, the sooner you’ll get fucked, but don’t come. Don’t forget, no coming.”Dean said.

“I’ll remember.”He said grinning as he watched the other leave. Settling in for a long night.

* * *

By morning light, Dean was regretting his resolve to stay put and watch the other. Swallowing hard as he leaned back on the bed, watching the other touch himself, moaning, whimpering and tormenting himself and Dean had to struggle not to touch himself. If Cas couldn’t come, neither would he, but it was hard watching him. 

“Dean?”

But Dean was already moving, already heading for the door before the other had managed to form his name in the morning light, hearing the distressed sounds he headed for the door. Carefully walking into the room he smiling quietly as he laid down over the other, carefully stroking heated flesh, but not touching his cock. Knowing cas’ cock would be tender and he needed to be gentle. “You were fantastic, so fantastic. Look how hard I am for you.”He moaned softly, looking at the other. “Such a good boy, what a good boy. You were perfect Cas, so perfect. Making all those naughty noises, playing with yourself so much, making me so hard. Teasing me.”Dean groaned.

“Deannnn…”Cas whined softly shivering at the praise, shuddering as the other settled on him more, feeling the other hard against his leg, moaning softly. Feeling the other pulling him into a tight hug, turning his head into the other’s shoulder.

“I’m here. I’m here.”Dean muttered pulling him tigher into a hug, holding him so tightly Cas could hardly move before breathing. “Come now, come for me, baby.”He muttered, his fingertips stroking the engorged length as he slipped the cock ring Cas was wearing off, holding him tight so he couldn’t hurt himself if he thrashed.

Cas gasped at the other, shuddering hard as he spilled out over the other’s arms, slumping bonelessly into his arms, utterly worn out and trembling in the aftermath.

“Shh, I have you now.”Dean muttered smiling quietly. “Yess…that’s it. Oh god, look how fantastic you are.”Dean moaned, grinding himself against the other, shuddering as he came himself, smiling quietly as he watched him. “That’s it, good boy. Such a good boy. Rest now. Sleep. I’ll watch over you.”He promised quietly, smiling softly at the boneless way Cas was simply laying in his arms. 

“kay.”Cas muttered already more then half asleep and simply letting Dean take care of him, sipping the juice when he was told before curling up against the other and sleeping.


	4. Chapter 4

Gabe paused at the sight of the man laying on the couch, watching him read for a few moments, simply enjoying the sight of Sam utterly relaxed. Smiling slightly at the sight of the comic the other was reading, well aware that it was Dean’s copy that the other was reading. “Shall we talk first, or are you finally going to get around to fucking me?”Gabe said before walking closer. “That the last one? It’s a shame they’re ending it.”

“Considering I’m here alone, I might be giving in and fucking you, you demanding bottom.”Sam said calmly returning to reading without looking at the other. For all the world, looking like he was planning on simply enjoying the other’s company. “You can talk, I need a foot rest while I finish reading.”He said well aware that Gabriel hated and loved being made to do menial labor. “And yes it is. It’s actually dean’s, but he’s putting off reading it, so I figured I can tease him into reading the end. And it really is good.”Sam said lifting his feet up to let the other kneel.

“I am a demanding bottom, you fucking cock tease.”Gabe complained, sulking as he grumbled about being used as furniture again. He hated it….it was humiliating…and probably why he loved it just as much. Being useful, being used, humiliated but making Sam pleased…it was a heady sort of pleasure and aside from his usual grumbles he settled into place. “He doesn’t want to read it?I thought he was obsessed?”

“Be glad I enjoy you being a demanding just as much as you enjoy my company. “He is. Which is why he doesn’t want it to end. If he does read it, it’s over. Though I think he’s going to enjoy Dean and Cas getting their shit together and having sex.”Sam snickered a little settlign his feet against the other’s back.

“Did they really?Shit. Now I wish I hadn’t left my copy at home.”

“Yea, apparently the author wanted it to go out with a bang. And you can burrow his.”Sam promised sighing quietly as he glanced down at the other. 

“Sam…I can’t keep doing this. You dance around me, over and over, but you never commit. I can’t do this anymore….it was fun, at first, the challenge, but I’m just tired now…I can’t keep waiting for you…my father is insisting I marry. I’m sure you understand that I need to know….will you be there for me if I refuse? Or will we be going our separate ways? Because if I refuse, I will have no where else to go. Everything I have, is tied into the Novak clan, and if I refuse the hand of the bitch my father chose, I will be cast out. Homeless, jobless, and helpless. I need to know Sam, because if your not there, then why should I bother?”Gabe said quietly. If Sam commited, then Gabe would to. If Sam didn’t….well, then he’d marry the airhead. Because he was selfish, himself came first, and if Sam wouldnt’ be there for him…then he’d be there for himself.

Sam frowned a little before setting down the book as he looked at the man at his feet. Going quiet as he reached out to draw the other up onto the couch next to him, tucking Gabriel under one arm, cuddling him. Hearing the other’s words, he needed to hold him, to talk about this. Not able to look at the other, not when he knew he was about to implode his whole life, because his emotional constipation was nearly as deep as Dean’s was, and while he could talk about things easier, surface emotions, the things he’d buried, were harder for him. The fact he’d been avoiding talking to anyone about how he felt for Gabe for five years, said whatever it was that kept him from getting involved, fucked with his head. 

“I’ll be there. I’m sure you know where me and Jess live.”He muttered because while he and Jess didn’t scene together usually on the island, they didn’t go out of their way to hide their marriage either. “If…if you want….to do this….we need to talk to Jess.”He said, sounding unsure, quiet. Which was uncommon in the lawyer who made a killing at ruling the room. The hesitance said he wanted Gabe, probably had wanted to be near him, and yet it screwed with him to. 

Gabe sniffled as the other hugged him, shifting to press his face into the other’s chest as he started to cry. He couldn’t hold it in anymore. He didn’t want to get married but he was frightened of his father. He couldn’t refuse to get married and still live under his father’s control or his father would beat the shit out of him. Gabe didn’t want to get married to that horrible bitch who wanted to control him. She told him who he could hang out with, who he could sleep with(her), and what his job could be. Where his father had dug her up from Gabe didn’t know, but he imagined he’d chosen the most domineering bitch he could find to make Gabe miserable. Cas’ father was at least pretending it was in Cas’ best interests and it was for cas’ own good. Raphael was just cruel and hated his son. 

“I can’t get married, and your the only person I can trust….sure Zar or Cas would shelter me, but they live under their father’s thumbs to, and I’d just get turned over again. I’m sorry if you feel like I’m blackmailing you into this, but….and I really like you, even if you wont fuck me, which I don’t get because I know you want to….you don’t have to decide now. We have a week…and if…if you decide that you can’t then I’ll talk to Crowley. He’d let me stay with him until I can get on my feet….but I’d rather…rather be yours. And I wanted you to know…you know, before I don’t have a chance.”

“Well I’m glad you trust me…and it’s not blackmail. Just desperation.”Sam muttered stroking the other’s hair, “Don’t worry I’ll make sure your dad leaves you alone…I will never understand you Novaks, they’re all a little weird.”He muttered before sighing. “It’s,…urgh. I hate these feelings talks but…you’re coming home with me.”he promised even as he shifted to snag his phone to text Jess, which rarely happened. They were usually religious about giving each other space when they were on the island. “Now. Do you want to read amazing smut and cuddle me, or go back to being my footstool while I do?”He added, eyeing the other. Another rarity, Sam rarely gave people choices in what he wanted to do.

“Thank you….”Gabe muttered having really been worried about how the talk would go. He knew Sam was married and hadn’t been sure how he’d handle Gabe setting down a ultimatum like that, but Gabe didn’t have time to mess around. Wincing a little because he knew he’d upset sam, because he knew sam hated the feelings talk. “I know…I’m sorry…can we just snuggle?”

“Yea, I’m more then okay with snuggling.”Sam said as he picked the other up, settling them into bed, settling gabe against him as he stroked the other’s hair, quietly reading. Simply settling in to rest, feeling nearly as wrung out as gabe looked.

* * *

Cas stirred, burrowing further under the nest of blankets he’d made for himself, shifting to look at the man as he looked for him. “….I thought you had class….did I miss it? Did I make you miss it? I’m sorry….I guess I needed more sleep then I thought…”Cas said sputtering to a stop after a moment.

“Hush Cas.”Dean ordered smiling at him as he made his way back to the bed, holding a plate of food. Fruits mostly, but with a few strips of bacon and french toast. “You should eat, scening takes alot of energy and what we did was extremely intense. The food will help you settle as your sugar levels come back up.”Dean promised watching the other. “You might be feeling much more emotional than usual so don’t feel worried if you react to things you normally wouldn’t even notice. You’re in a heightened emotional state right now and both physically, mentally, and emotionally sensitive at the moment. As for my class, it’s not another two hours and I would have woken you if I ran the risk of being late. A good dom will NEVER leave a sub after a scene like that, and if I had been unable to tender care to you, I would have ensured you were with Zar, or Crowley, so that they could make sure you were content and cared for.”Dean paused studying the man who was looking thoughtful and quiet as he nibbled on his food. “I might have left you with Sam, but he’s big and imposing and I’m not sure how you’d react to him in this state. Now, how are you feeling? Any bad feelings or sensations? Pain, feeling hurt, or upset?”

“I feel….unsettled is a good word for it.”Cas muttered remembering what Dean had said about talking, and since the other had been so kind to him, he knew he needed to try and at least talk more then he normally did. “Zar would have been a good choice if he wasn’t busy…”Cas said, even if he might tease his cousin about getting him in trouble, he knew Zar would look after him. Looking relieved at the knowledge though that he hadn’t missed the class he thought about how he was feeling. “Unsettled….off. Like I should spend the day in my studio instead of interacting with anyone, but calm enough to interact without being bitchy if I had to….if that makes sense. I feel….less exposed and hyper aware than I was earlier so that’s good….overall, I think I’m okay.”

“Unsettled is usual. It’s your first drop so it’s going to feel off and make you feel off kilter and uncertain.”Dean promised. “sort of like the world’s tilted to the side a little and your not sure which way is up. Is that a little how it feels?”

“Exactly….like the floor’s slanted, not quite right.”Cas nodded a little thinking about that, frowning slightly. Worried about how he was going to react to all of this though at the moment he felt, while off kilter, fairly steady despite that.

 

“It’s not uncommon for a sub coming up from a sub space to cry, get hyper, become aggravated or even depressed depending on their own personal experience and what they did….everyone reacts differently and there’s no right or wrong feelings as you start coming up, but if you get upset, depressed, unhappy or other various ‘bad’ emotions, you should be sure to stay with a dom who can care for you because those emotions can get worse and not good. It’s normal to feel them but that doesn’t mean you should go through it alone because normal sadness or self loathing can easily become self harming, even if its only in your head that can become very serious. So if you ever find yourself feeling as if your disgusting or as if your not worth it. Find a dom you trust immediately, or a sub can help to, because you are not disgusting, you’re not abnormal, and you’re not always worthwhile and deserving of affect and care.”Dean promised watching him. “And if you feel like you need to be alone, that’s okay to. Some subs don’t like being around other people while they come back up. Like I said, everyone reacts differently. Now eat, drink your coffee. As you start coming up, you should start feeling your emotions leveling out.”

“I’ll remember that. Find someone.”Cas muttered reassuring dean that he understand, because even if Dean didn’t know him, those who did would be well aware he would usually simply retreat into being alone and quiet to deal with anything. Sipping his coffee he smiled at the order. “I am. See, eating and all.”Cas said well how about that. A sassy coming up sub. The fact that he was normally a sassy asshole just was made worse when his usually mind-to-mouth filter was out of commission to due his current state. “You have a class? I mean….something I could draw?I want to come but…”He twitched slightly, wanting to draw. Wanting to settle in with his tablet and work, but not sure if he’d be allowed to.

“I do have a class.”Dean admitted grinning at the utter sass from the other. “And yes, actually it is something you could draw. It’s shibari, Japanese art bondage. It’s one of my favorites. Shibari is bondage meant to be held for hours comfortably and people who like to feel completely helpless particularly enjoy it. Personally I’m just artistically inclined and I like seeing a sub so beautiful… it’s a longer class than most because it’s really popular, it’s going to be my first year teaching….I hope I do okay…”Dean said watching him. “I take it drawing helps you feel settled into your skin? That’s good. If you like, you can come with me to talk to Ellen. She’s going to be my helper. You can ask her personally if it’s alright for you to draw her.”

“...sounds perfect for drawing then, no one will be moving for a bit.”Cas said taking it more from a artist’s headspace, then sexual at the moment, his thoughts already turning over how to draw it the best. “Considering I spend most of my life drawing, yes it makes me feel better.”Cas snarked as he leaned across his bed to retrieve his bag, pulling it up onto the bed with him so he could make sure he had both his drawing pad and his good markers, even if he hadn’t touched it since he’d gotten there the night before, he still needed to make sure all his stuff was there. “I’ll come with you, let me get dressed.”

“It can be very intense even if there’s no sexual components to it. Ellen, has a huge bondage fetish. She says the ropes are like holding her together, trapping her inside herself so she can’t spill out, makes her feel safe. Comforted. She’ll spend the entire class down so deep that she wont react to external stimulation. She’s the kind of sub who has to be watched, that’s why she has a red collar, because she can’t be trusted with her own safety.”Dean explained watching the other getting ready to go. “She has no limit, and she almost died before because of mishandling….she’s one of the few people who can get through a three to five hour class without having to break. Because once the ropes go on, she completely relaxes.”

“Makes sense.”Cas said thinking that over as he got dressed, a little hyper now that he knew he could do what he wanted. Tugging on the skinny jeans and tugging them into place, before sliding on a button up dress shirt but not bothering to button it up. If everyone else was going to wander around half dressed, he might as well enjoy it himself. “Okay, we can go.”

“Let’s go then.”Dean grinned as he reached out to tug the tag off the other’s collar. “I have to take this back. It’s considered improper to wear it while I’m teaching, and I’m sure you want to explore a bit. I’d highly recommend a threesome with Jess and Lisa, you’ll never look at women the same way again.”Dean said as they walked towards the classroom.

“I might do that though considering how much shit I’ve put them both through sometimes, I might not want to get naked near them.”Cas snickered as he bounced along with him.

“You know, you might be right. They tend to be a bit devious, and I’m not saying that because me and lisa used to be together. She’s wicked.”

“They are.”Cas snickered a little going quiet as they walked.

“So you’re a artist then?”He asked, remembering the other’s words about spending a lot of time drawing. “I’m a dog breeder myself, if you can believe that.”

“Yes I am.”Because no matter what he was going to be doing for the rest of his life, he was a artist first. “Really?I can see it. Very in command you are.”He teased.

“I like being in command. I’ve actually gotten dogs for Zar and Gabe. They came in and picked out a dog for their favorite cousin. One of my more interesting breeds, a Xoloitzcuintli. Very well behaved and one of the more…mischievious ones.”

“.…You’re the reason I have to put up with Princess?Thanks, dean.”Cas whined a little before startling. “Loi? Yea, he’s fairly mischievous and underfoot all the time…it’s probably a good thing I work from home otherwise my house would be a prank filled mess from my dog.”

“Yes, yes I am.”Dean snickered a little at the mention of Gabe’s yippy little yorkie, before grinning. “You’re the one that Gabe and Zar got him for? Perfect. He made me promise not to do a background on you, not sure why, but I trust him so I didn’t. I usually do for anyone who gets one of my puppies…. you named him Loki then?He’s doing well?”

“Yea. Apparently having a dog makes them think I’ll leave my house more then I do. Though I left more than they thought I did. Or lisa thinks I do.”Cas made a face, grumbling a little. “Yes, I named him loki. He’s doing well, gets along amazingly with my cat actually. They spend alot of time pranking each other while I’m working, so it works.”

“Huh…you know, I have hundreds of dogs and I never go anywhere. In any case, Lisa thins anyone who spends more then eight hours inside is working to much and needs to go outside more. She’s a bit biased that way, she can’t say much to me though, because even if I work fifteen hours a day, it’s mostly outside and with other people…..and a cat? They didn’t tell me you had a cat. That could have been a problem, I should scold them for not telling me you had a cat….they’re lucky I have you loki since they mentioned you might get more pets.”It was amazing that Dean had remembered all that about a dog he’d given to Gabe and Zar a year ago.

“Sorry. Don’t yell at them, they didn’t know I had a cat at the time, but Loki and Wyvern get along amazingly.”

“How are you handling Loki’s energy?”Dean asked, curious. Xoloitzcuintli were exceptionally high energy breeds.

“Well. Lots of walks and playing with Wyvern help.”

“You named your cat Wyvern….I’m afraid to ask why.”Dean chuckled. “I have a feeling you’ve been the victim of a few kamikaze dives.”

“Wyvern thinks she can fly, and routinely tests her skills on houseguests.”He grinned as he dug out his wallet to show the other the picture of his pets. As proud of his animals as any parent would be. Well aware his part savannah cat thought the house belonged to her.

“Oh my god, you have one of those monsters. Yea, in that case Loki’s no problem for you.”Dean snickered amused. “One of these days you should come to Winchester Farms. Gabe and Zar visit alot, you could tag along. I think you’d love seeing all the dogs.”Dean said feeling like he never wanted to let the other go, which was weird. He’d never felt that way before.

“Maybe I will.”Cas smiled slightly at the idea as they walked into the classroom.

“Hello Ellen.”Dean said gesturing to the hyper black haired ball of energy walking next to him. “Ellen, this is Cas. Cas, Ellen. He wanted to ask you something.”

“Oh?”

“H-hello. I-I wanted to ask-”Cas stuttered shifting, a little nervous to ask. “I was wondering if you would mind if I drew you while I attended class….dean said he was okay with it but I wanted to ask you to…”

“Draw me? No one’s ever wanted to draw me before….may I keep the drawing?”Ellen asked hopefully. “I’d like to have one. I’ve never seen myself like this before. It sounds exciting.”

“She doesn’t like cameras. They’re to impersonal, and she doesn’t like the way they seem dead.”Dean explained. “Drawings aren’t like that though”

“Cameras are so impersonal, but drawings have so much life and heart and personality. I’d really like it if you drew pictures of me.”Ellen promised.

“Yes, I would like to. It helps me relax and…and I remember things better, experience them more, if I draw them.”Cas perked up brightly at the idea that he was going to get to do this. “And yes, if you want, you can keep it.”He promised. Grinning as he settled in to work.


	5. Chapter 5

“Sam?”Jess asked as she stepped into the living room, pausing in the bedroom door as she watched them. Unsure if she was to enter with Gabe snuggled up against him. Island time was private time, and she didn’t want to interrupt if Sam had gotten distracted and forgot he’d asked her to stop by.

“Come on in.”Sam said startling a little at the sound of her voice, offering her a small strained smile. Usually he enjoyed talking with Jess, and the only time he got fidgety was when he knew he’d done something wrong and didn’t want to tell her but knew he had to.

“Alright….what did you do?”Jess said, narrowing her eyes at him as she walked closer. She knew that expression, and being a switch, dominantly sub, she recognized the position they were in. Gabe was a upset sub and Sam was the slightly overprotective dom at the moment, easing down into the chair next to the bed, resting a hand on his knee. “Sam? What is it?”

Sam smiled quietly, looking up at her, relaxing under the touch. Ducking his head a little, she wasn’t mad with him, he didn’t want to tell her anything. Didn’t want to upset her, but simply being with him was enough to make him relax. “…I want to take him home. Gabe needs a place, and…I don’t want to let him go anywhere else…I want to keep him and take care of him, and I’m sorry. I know I shouldn’t, but I want to…Jess I’m sorry…”Sam stared down, looking so lost and confused, hurting because he knew it was going to hurt his wife that she wasn’t enough for him. At least, that was his thinking, that he never wanted her to feel like she wasn’t enough, because she was. She was everything he’d wanted as a kid, had always been what he wanted….but he wanted Gabe to.

 

“What brought this on?”Jess said watching him, not even looking surprised. Wondering what really had her husband so upset, before looking amused. 

“.…you sound amused. Why are you amused?”Sam muttered frowning a little.

“Sam….oh Sweetie….you idiot. I always knew you wanted to bring Gabe home. You’ve been half in love with him since the first year he came here. Did you really think I would be angry with you having a boyfriend, when I have a girlfriend? Of course he can come live with us, so long as he understands that I get attention to.”jess said looking worried as she studied Gabe. “Why now though? He looks terrible.”She wondered, worried about what had to driven GAbe, because she knew it had to be have been Gabe, to make such a move. 

“You.…have a girlfriend?”Sam chewed on that for a moment, “Lisa?….I’ll make sure he knows that. Though he knows we’re married, I don’t think he’d be surprised I’m going to stay with you to.”Sam said looking bemused, a little confused. This wasn’t….normal. He was breaking the rule about just one week of being free. Wasn’t she upset? “HIs father ordered him to get married. He doesn’t want to, but if he doesn’t, he loses everything. So he’s going to come home with us.”

“Wait….you didn’t know?!”Jess looked startled, staring at him. “Sam, I’ve been dating Lisa for years. How did you not notice?! I talked to you about it.”Jess said before pausing. “Oh. Wait. I knew I forgot something….still, how did you not notice?”she said drawing a harsh breath in. “Definitely coming home with us then.”She decided.

“.…You’re friends!I mean, I knew you guys do stuff here but…I thought that was it…I mean…you guys are dating?”Sam said, voice small and genuinely confused rather then upset. 

“Oh, sam, baby….you’re so emotionally constipated.”Jess said sounding amused as she kissed his forehead. “Yes, we’re dating. We’ve been dating since you and Dean introduced us. I really thought you knew….dean knew, but he probably thought you knew to.”

“Am not.”

“Are to.”

“Sam….?”

Looking down he growled softly, protectively. “It’s okay. I’m sorry. It’s just Jess. Didn’t mean to wake you up.”Sam muttered.

“Jess…”Gabe asked sluggishly as he snuggled back down into Sam’s side now that he knew it was okay, that he was safe. “’s she mad? I’m sorry.”Gabe mumbled as he tucked his head against Sam’s chest.

“No, I’m not mad….The poor thing, he’s exhausted.”Jess sighed stroking Sam’s hair. “I’ll get you both some breakfast. Stay with him.”She said smiling at her husand. “And just so we’re clear, I approve of bringing Gabe home. I might even enjoy it.”

Sam stared after his wife, looking so utterly bemused.

* * *

“.…So, I can come home with you?”gabe said looking hopeful as he glanced at both winchesters as Sam sat up to eat. “Does this mean your finally gonna fuck me?Cause I really wanna get fucked, ‘specially if I help you with your deep impact seminar.”

“I will….and when I do fuck you, and when I decide. I’m not going to be rushed, now that we’re going to do this.”Sam said smiling softly. 

“Shouldn’t she be mad at me for imposing?”Gabe asked, he’d been most worried about her being angry that he was trying to steal her husband. Which he sort of was, though he was hoping for equal shares. He didn’t want all of Sam’s attention, god he wouldn’t be able to handle that after being alone for most of his life. 

“Well, I had thought she would be, but I’ve been informed she has a girlfriend, and has been waiting for me to get my shit together and invite you home. So here you are. Coming home with me, and Jess.”Sam said, babbling a little. While he might be a dom, might spend most of his life in icy control of himself but when he let the grip loosen a bit, especially when it involved emotions, he babbled some as he sought to control himself again. Usually it ws only around Jess that he allowed the walls to fall, or if he was on the island, sometimes, with Dean.

 

“So….I had a idea for tonight. I hope you don’t mind being my date for the evening, Jess.”Sam said as he ate, looking up when Lisa and jess walked in.

“Date?”Jess asked surprised. Sam had never broached the subject of them doing things together on the island, though htey had. The threesome and foursomes with Sam, her, Lisa, and Dean were always intense and very very fun. This was new. “You mean to the ball?”

The ball was a new event, Crowley had introduced. A big masquerade ball where you could dance and drink and have fun. It had been proven to be a very popular idea. 

“I’m not going! I hate dancing!”Gabe declared.

“You’re going.”Both Lisa and Jess said.

“You’re not the boss of-”

“Your going, or I’m going to get a chastity belt and you’ll not get to fuck my husband until we’re off the island.”

“I’m going.”

“That’s what I thought.”

“...Now I have to find a costume…”Gabe sulked a little watching the others for a moment, trying to decide what he should wear.

Sam laughed a little before smiling at his wife. “Yes. I, uh. Have a present for you to.”Sam said as he eased away from Gabriel to get into his closet. “So. Well, before you decide to go with me though, you should see what you’re wearing, just in case you decide you’d rather go as Lisa’s date.”

Digging through his bag for a moment to draw it out, the black corseted dress was beautiful, and a sheer so finely woven that she was going to be naked otherwise though the fine black threads, except…. there was a king’s ransom worth of blue diamonds sown into it, so it was a utter sparkled beauty. A fortune simply sown to make her shine, though the corset part was the only real diamonds, the rest were beautiful glass through the skirt, she was still wearing a fortune, not that that was the true appeal of the dress to Sam. The fact that the fabric was utterly see through and she was going to be naked under it was secondary to the fact that for Sam, who had so many problems showing he cared, of making sure Jessica knew her value to him, he’d done the only thing he could. Show her she was worth more then anything else to him. It had been something he wanted, a passing thought to dress her like a king’s concubine. “Well?”Sam muttered offering her a small shy smile, worried she wouldn’t want to go with him, since he was breaking their normal rules about the island.

 

Jess’ eyes went wide as she stared at the dress, before lunging for her husband, slamming their lips together in a desperate kiss. “I fucking LOVE you.”She breathed before turning her attention to the dress again. “I love it. It’s gorgeous, perfect. I’m going to look like the most expensive concubine…I’m so sucking your dick later.”Jess informed her husband.

“Surely it deserves more then a blowjob?”Gabe snickered a little.

“Nope, he gets a blowjob, and a dance.”Jess decided with a smile, stroking the dress, practically infatuated with it as she sat down on the bed. 

“I’ll look forward to it.”

“Better watch out Sam, she might decide to marry the dress.”Lisa teased.

Sam grinned brightly at her praise, watching her. “I wouldn’t be surprised if she tried marrying the dress.”Sam said as he reached down to adjust himself, hard and aching at her response to the dress and while it was bothersome, he was to happy at the moment to do something about it.

“Maybe if you ask nicely, Gabe will take care of that for you.”Jess said smirking a little as she flounced off to the bathroom to try on the dress.

“.…Seriously. You’ve been a cock tease for five years, I’m not helping you with that.”Gabe admitted as he leaned over to snag the supernatural book off the nighstand, settling in to read.

Sam grinned looking amused as he leaned down to press a kiss to the other’s forehead. “Fine by me. Enjoy the book, I’m sure I can find someone willing to help me with this.”he said stealing a kiss before leaning back to see how the other was really. “I’m going to go see how Dean’s doing, you okay by yourself?”

“I’ll be fine. I worked myself up a lot this last week..I need to decompress, and Jess and Lisa are here if I need something.”Gabe said smiling a little as he could hear the women in the bathroom talking, before settling in to read as Sam left. Lounging around in a place he knew was safe, and knowing he had somewhere to go, went a long way to sooth jangled nerves.

**Notes for the Chapter:**

> hey guys, just saying hi. and wanted to let you know, I am totally working on each chapter, but reviews and knowing people are reading it, will always make me work faster, so yes, let me know!It's always good to know it's been appreciated.


	6. Authors note

Sorry guys not a real chapter but I wanated to put this out there. I promise I'm working on it, have been for two months but my dads seriously sick and in the last few weeks took a serious turn for the worse and just.... it's bad guys and by the time I sit down I'm in no mental space to write awesome dean/cas moments and give it that special feel when all I want to do is hold up for awhile with a good book, a few episodes and supernatural and pretend my world hasn't just gotten scarier without my dad... he's not gone yet but it's getting there and despite years to prepare... I'm not ready. So please, please hang in there and I promise I'll post


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